Salt and pepper the chuck roast on all sides. Bring one tablespoon oil to almost smoking over medium-high heat in a Dutch oven or similarly sized heavy bottomed pot. Brown the roast on all four sides, about 3 minutes per side, and transfer to a plate.
Add the remaining oil to the pot, along with the bell peppers, onion, jalapeño and a pinch of salt. Cook over medium heat until the onions are translucent and it’s all just begun to caramelize, about 10 minutes. Add garlic, cumin, oregano, paprika and cloves and cook for another minute.
Add sherry and give a good stir, getting any crispy bits off the bottom of the pan. Add the diced tomatoes and the bay leaves and return the roast to the Dutch oven and the stovetop, reduce the heat to low and cover. Cook for 3 to 4 hours, until the roast has become tender and is easily broken up with a fork.
Remove the bay leaves from the pot. Shred the meat using two forks and add the olives, capers, and two tablespoons cilantro. Let simmer over medium heat for ten minutes before serving.
Assemble your tacos with a heaping spoonful of the shredded beef, followed by cotija, cilantro, and lime.